US11014995B2 - Procatalyst composition made with a combination of internal electron donors - Google Patents
Procatalyst composition made with a combination of internal electron donors Download PDFInfo
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- US11014995B2 US11014995B2 US16/334,420 US201716334420A US11014995B2 US 11014995 B2 US11014995 B2 US 11014995B2 US 201716334420 A US201716334420 A US 201716334420A US 11014995 B2 US11014995 B2 US 11014995B2
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- 0 [1*]C1=C(OC(C)=O)C(OC(C)=O)=C([4*])C([3*])=C1[2*] Chemical compound [1*]C1=C(OC(C)=O)C(OC(C)=O)=C([4*])C([3*])=C1[2*] 0.000 description 13
- YCPTZKSDUKDVKA-UHFFFAOYSA-N O=C(OC1=CC=C2C=CC=CC2=C1OC(=O)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound O=C(OC1=CC=C2C=CC=CC2=C1OC(=O)C1=CC=CC=C1)C1=CC=CC=C1 YCPTZKSDUKDVKA-UHFFFAOYSA-N 0.000 description 2
- WCWHLXYMRAOGCV-UHFFFAOYSA-N CC1=CC(C(C)(C)C)=CC(OC(=O)C2=CC=C3C=CC=CC3=C2)=C1OC(=O)C1=CC2=C(C=CC=C2)C=C1 Chemical compound CC1=CC(C(C)(C)C)=CC(OC(=O)C2=CC=C3C=CC=CC3=C2)=C1OC(=O)C1=CC2=C(C=CC=C2)C=C1 WCWHLXYMRAOGCV-UHFFFAOYSA-N 0.000 description 1
- RXPRTCODVUACBB-UHFFFAOYSA-N CC1=CC(C(C)(C)C)=CC(OC(=O)C2=CC=CC3=C2C=CC=C3)=C1OC(=O)C1=C2C=CC=CC2=CC=C1 Chemical compound CC1=CC(C(C)(C)C)=CC(OC(=O)C2=CC=CC3=C2C=CC=C3)=C1OC(=O)C1=C2C=CC=CC2=CC=C1 RXPRTCODVUACBB-UHFFFAOYSA-N 0.000 description 1
- XKUSNQSAFFZWMS-UHFFFAOYSA-N O=C(OC1=CC2=CC=CC=C2C=C1OC(=O)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound O=C(OC1=CC2=CC=CC=C2C=C1OC(=O)C1=CC=CC=C1)C1=CC=CC=C1 XKUSNQSAFFZWMS-UHFFFAOYSA-N 0.000 description 1
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- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/04—Monomers containing three or four carbon atoms
- C08F10/06—Propene
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- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
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- C08F110/06—Propene
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- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/647—Catalysts containing a specific non-metal or metal-free compound
- C08F4/649—Catalysts containing a specific non-metal or metal-free compound organic
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
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- C08F4/00—Polymerisation catalysts
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- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
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- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
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- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/654—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof
- C08F4/6543—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof halides of magnesium
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/65—Pretreating the metal or compound covered by group C08F4/64 before the final contacting with the metal or compound covered by group C08F4/44
- C08F4/652—Pretreating with metals or metal-containing compounds
- C08F4/654—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof
- C08F4/6543—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof halides of magnesium
- C08F4/6545—Pretreating with metals or metal-containing compounds with magnesium or compounds thereof halides of magnesium and metals of C08F4/64 or compounds thereof
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65916—Component covered by group C08F4/64 containing a transition metal-carbon bond supported on a carrier, e.g. silica, MgCl2, polymer
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- C08F2410/00—Features related to the catalyst preparation, the catalyst use or to the deactivation of the catalyst
- C08F2410/06—Catalyst characterized by its size
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/12—Melt flow index or melt flow ratio
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- C08F2500/15—Isotactic
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- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/646—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64
- C08F4/6465—Catalysts comprising at least two different metals, in metallic form or as compounds thereof, in addition to the component covered by group C08F4/64 containing silicium
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Definitions
- preferred cocatalysts are selected from triethylaluminum, triisobutylaluminum, tri-n-hexylaluminum, diisobutylaluminum hydride, and di-n-hexylaluminum hydride, with the most preferred cocatalyst being triethylaluminum.
- the second internal electron donor has been found to increase the efficiency of incorporation of the first internal electron donor into the procatalyst composition.
- greater amounts of the first internal electron donor are incorporated into the procatalyst composition when the second internal electron donor is present. Consequently, less of the first internal electron donor is consumed and/or wasted during the process of making the procatalyst.
- the magnesium procatalyst precursors may be formed into uniform particles through various methods known in the art. Several of these methods are described, inter alia, in U.S. Pat. Nos. 5,468,698, 5,476,824, 5,905,050, 4,315,835, 4,469,648, 4,399,054, 6,127,304, 5,082,907, 5,066,737, 4,442,276, 4,540,679, 4,547,476, 4,460,701, 4,829,037, 5,028,671, 5,247,031, and elsewhere which are incorporated herein by reference.
- any consecutive R groups in R 1 -R 4 , and/or any consecutive R groups in R 5 -R 9 , and/or any consecutive R groups in R 10 -R 14 may be linked to form an inter-cyclic or an intra-cyclic structure.
- the inter-/intra-cyclic structure may or may not be aromatic.
- the inter-/intra-cyclic structure is a C 5 or a C 6 membered ring.
- the external electron donor and/or activity limiting agent can be added into the reactor separately.
- the external electron donor and the activity limiting agent can be mixed together in advance and then added into the reactor as a mixture. In the mixture, more than one external electron donor or more than one activity limiting agent can be used.
Abstract
Description
wherein R1-R14 are the same or different. Each of R1-R14 is selected from hydrogen, a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof. At least one R1-R14 is not hydrogen. Particular examples of the first internal electron donor are 3-methyl-5-tert-butyl-1,2-phenylene dibenzoate and 3,5-diisopropyl-1,2-phenylene dibenzoate.
where R1, R2, R3, and R4 are the same or different, methyl, C2-C18 linear or branched alkyls, C3-C18 cycloalkyls, C4-C18 cycloalkyl-alkyl, C4-C18 alkyl-cycloalkyl, phenyl, organosilicon, C7-C18 arylalkyl, C7-C18 alkylaryl radicals; R1 or R2 may also be a hydrogen atom.
where R1 through R6 are as described for R1 through R4 of the structure above. R1 through R4 may optionally be a hydrogen atom or combined to form one or more C5-C7 fused aromatic or non-aromatic ring structures, optionally containing an N, O, or S heteroatom. Particular examples of the second internal electron donor include 4,4-bis(methoxymethyl)-2,6-dimethyl heptane, 9,9-bis(methoxymethyl)fluorene, or mixtures thereof.
where R1-R4 are the same or different, each of R1-R4 is selected from the group consisting of hydrogen, a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof, and at least one of R1-R4 is not hydrogen; and
at least one or two, or three, or four R groups of R1-R4 is selected from a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof, and where E1 and E2 are the same or different and selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl or an inert functional group optionally containing heteroatoms wherein all have from 1 to 20 carbon atoms.
wherein R1-R14 are the same or different. Each of R1-R14 is selected from hydrogen, a substituted hydrocarbyl group having 1 to 20 carbon atoms, an unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof. At least one R1-R14 is not hydrogen.
where R1, R2, R3, and R4 are the same or different, methyl, C2-C18 linear or branched alkyls, C3-C18 cycloalkyls, C4-C18 cycloalkyl-alkyl, C4-C18 alkyl-cycloalkyl, phenyl, organosilicon, C7-C18 arylalkyl, C7-C18 alkylaryl radicals; R1 or R2 may also be a hydrogen atom.
where R1 through R6 are as described for R1 through R4 of the structure above. R1 through R4 may optionally be a hydrogen atom or combined to form one or more C5-C7 fused aromatic or non-aromatic ring structures, optionally containing an N, O, or S heteroatom.
TABLE 1 |
Bulk polytests with DCDMS external donor |
Activity | MFR | XSRT | |||
Catalyst (mg) | (Kg/g-cat*h) | (g/10 min.) | (wt %) | ||
Exp-1 (2.15) | 88 | 58.8 | 1.72 | ||
Exp-2 (2.50) | 81 | 68.9 | 1.44 | ||
Exp-3 (2.05) | 93 | 73.7 | 0.99 | ||
C1 (2.40) | 92 | 10.8 | 1.35 | ||
C2 (2.95) | 77 | 175.2 | 3.34 | ||
C3 (4.50) | 63 | 17.0 | 1.77 | ||
TEAI/DCDMS = 15, H2 charge = 188 mmol. |
TABLE 2 |
Bulk polytests with CMDMS external donor |
Activity | MFR | XSRT | PDI | |||
Catalyst (mg) | (Kg/g-cat*h) | (g/10 min.) | (wt %) | (Pa) | ||
Exp-1 (3.00) | 90 | 3.2 | 1.28 | 4.6 | ||
Exp-2 (2.70) | 89 | 6.4 | 2.54 | 4.6 | ||
Exp-3 (2.60) | 106 | 6.1 | 0.98 | |||
C1 (2.55) | 90 | 1.5 | 2.22 | 5.3 | ||
C2 (2.50) | 77 | 23.5 | 4.00 | 3.8 | ||
C3 (5.20) | 48 | 5.3 | 2.20 | 4.3 | ||
TEAI/CMDMS = 15, H2 charge = 68 mmol. |
Claims (20)
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PCT/US2017/053863 WO2018067367A1 (en) | 2016-10-06 | 2017-09-28 | Procatalyst composition made with a combination of internal electron donors |
US16/334,420 US11014995B2 (en) | 2016-10-06 | 2017-09-28 | Procatalyst composition made with a combination of internal electron donors |
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EP (1) | EP3523343A4 (en) |
JP (1) | JP7113817B2 (en) |
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CO (1) | CO2019003176A2 (en) |
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CN108239191B (en) * | 2016-12-23 | 2019-10-01 | 北京利和知信科技有限公司 | A kind of alkoxyl magnesium carrier model catalyst component for olefin polymerization, catalyst and its application |
KR102156075B1 (en) * | 2019-03-11 | 2020-09-16 | 효성화학 주식회사 | Ziegler-Natta procatalyst compositions AND OLEFINE polymerization process |
CN110144022B (en) * | 2019-05-28 | 2020-02-21 | 国家能源集团宁夏煤业有限责任公司 | Industrial preparation method of Ziegler-Natta catalyst |
KR20220085772A (en) * | 2019-09-18 | 2022-06-22 | 더블유.알. 그레이스 앤드 캄파니-콘. | Catalyst compositions and systems with extended lifetime |
CN114085301B (en) * | 2020-06-29 | 2023-05-09 | 中国石油化工股份有限公司 | Solid catalyst component for preparing olefin polymer and application thereof |
Citations (42)
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KR20190065368A (en) | 2019-06-11 |
JP2019529673A (en) | 2019-10-17 |
CN110023351B (en) | 2022-04-26 |
CO2019003176A2 (en) | 2019-06-19 |
RU2019113132A3 (en) | 2020-12-23 |
KR102461635B1 (en) | 2022-10-31 |
BR112019007032A2 (en) | 2019-07-09 |
EP3523343A1 (en) | 2019-08-14 |
SA519401473B1 (en) | 2022-11-14 |
RU2019113132A (en) | 2020-11-06 |
RU2752084C2 (en) | 2021-07-22 |
EP3523343A4 (en) | 2020-05-13 |
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JP7113817B2 (en) | 2022-08-05 |
CA3038093A1 (en) | 2018-04-12 |
WO2018067367A1 (en) | 2018-04-12 |
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